New nitrosamine-alkali-salts of halogenated and methyl-substituted amines



Patented Aug. 13, 1929.

UNITED STATES GERMANY, 'ASSIGNORS TO GENERAL N. Y., A QOBPORATION OF DELAWARE.

PATENT OFFICE.

ANILINE WORKS, INC., OF NEW YORK,

NEW NITROSAMINE-ALKALI-SALTSCF HALOGENATED AND METHYL-SUBSTITUTED AMINES.

No Drawing. Application filed December 16, 1927, Serial No. 240,633, and in Germany'neceinber 31, 1926.

In our copending application, Serial No. 240,632, filed on the same date an improved process for manufacturing alkall metal salts of nitrosamines of primary aromatic ammes is described, which process comprises introducing the syndiazotate prepared at lower temperatures into a sufiiciently concentrated caustic alkali solution and taking care, that the temperature of the reaction mixture permanently is not less than the temperature of a conversion into the antidiazotate.

Our present invention relates to certain new nitrosamine alkali salts of halogenated and methylsubstituted anilines, unknown hitherto, which are obtainable by the aforesaid improved process with an excellent yield I and in a very pure state, of which the following isanillustrative example in which the parts are by weight and all temperatures are in centrigrade degrees.

Example.

' in QOO-parts of water. In this manner with an excellent yield the potassium salt of the nitrosamine of 5-chloro-12-toluidine corresponding probably to the formula:

is obtained. It is a new compound unknown small leaflets.

hitherto and represents light reddish small prlsms. In the same manner at a temperature of conversion of about 110 a flesh colored potassium salt of the nitrosamine of 4-chloro-- 1.2-,toluidine is obtained, which crystallizes in The nitrosamines of 5.6- dichloro-lJZ-toluidine and 2.6-dichloro-1- amino-1.3-xylene require a temperature of converision of about 120. Their potassiunf salts represent light fleshwcolored small needles and reddish small crystalline granules respectively, that of 4l-bromo-2 toluidinenitrosamine light lamellas, that of 5-chloro-2- bromo-1.4-toluidine almost colorless lamellas.

The alkali salts of the nitrosamine of 4achloro-1.3-toluidine represent an orange colored crystal powder, of 4.5-dichloro-12- toluidine light fresh colored small crystals, of 2 5 dichloro 1.4 toluidine yellowish needles, of 2.3-dichloro-1.ektoluidinereddish" needles, of 6chloro-1.2-toluidine light fleshcolored small crystals. All these nitrosamines are new compounds.

We claim: 1. As new componds the alkali salts of nitrosamines of halogenated and methylsubstituted anilines, being when dry yellowish to reddish to brownish crystalline substances and corresponding probably to the formula:

wherein a: is the number 1, 2 or 3 and y the number 1 or'2 and wherein Hal represents a halogen and Me represents an alkali metal.

2. As new compounds the alkali salts of nitrosamines of halogenated ortho-toluidines, being when dry yellowish to reddish to brownish crystalline substances and corresponding probably to the formula:

being when dry yellowish to reddish to brownish crystalline substances and corresponding probably to the folmula:

Me p N/ \NO wherein the benzene nucleus may contain further chlorine atoms and Me represents an alkali metal.

In testimony whereof, we afiix our signa- 

